Levocetirizine

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Levocetirizine
Levocetirizine structure 2.svg
Ball-and-stick model of the levocetirizine molecule
Systematic (IUPAC) name
2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Clinical data
Trade names Xyzal, Levazyr
AHFS/Drugs.com Monograph
MedlinePlus a607056
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration
Oral
Legal status
Legal status
Pharmacokinetic data
Bioavailability High
Protein binding 90%
Metabolism Hepatic 14% CYP3A4
Biological half-life 6 to 10 hours
Excretion Renal and fecal
Identifiers
CAS Number 130018-77-8 N
ATC code R06AE09 (WHO)
PubChem CID 1549000
IUPHAR/BPS 1214
ChemSpider 1266001 YesY
UNII 6U5EA9RT2O YesY
KEGG D07402 YesY
ChEMBL CHEMBL1201191 N
Chemical data
Formula C21H25ClN2O3
Molar mass 388.888 g/mol
 NYesY (what is this?)  (verify)

Levocetirizine (as levocetirizine dihydrochloride) is a third-generation non-sedative[citation needed] antihistamine, developed from the second-generation antihistamine cetirizine. Chemically, levocetirizine is the active enantiomer of cetirizine. It is the R-enantiomer of the cetirizine racemate. Levocetirizine is an inverse agonist that decreases activity at histamine H1 receptors. This in turn prevents the release of other allergy chemicals and increased blood supply to the area, and provides relief from the typical symptoms of hay fever. It does not prevent the actual release of histamine from mast cells.

The manufacturers claim it to be more effective with fewer side effects than the second-generation drugs; however, there have been no published studies supporting this assertion. A study part-funded by the manufacturer UCB concluded it may be more effective than some other second- and third-generation anti-histamines, but didn't compare it to cetirizine.[1]

History[edit]

Levocetirizine was first launched in 2001 by Belgian pharmaceutical company UCB.

Brand names[edit]

It is sold under the brand names:

  • Xyzal /ˈzzæl/ in Australia, Austria, Croatia, Czech Republic, Finland, France, India, Ireland (also Rinozal), Lithuania, Netherlands, Portugal, Romania, Taiwan, Turkey, The Philippines, Serbia, Slovakia, Slovenia, South Africa and UK. On May 25, 2007, the United States Food and Drug Administration approved Xyzal, where it is co-marketed by Sanofi-Aventis.
  • Xusal in Germany;
  • Xozal in Greece;
  • Cezera in Poland;
  • Xazal in Spain;
  • Xuzal in Mexico;
  • In Hungary it is marketed as Zilola (made by Richter Gedeon) and Histisynt (Actavis).
  • In India, levocetirizine is marketed by GlaxoSmithKline under the brand name Vozet. Torrent Pharma launched UVNIL for the rural market.
  • In Pakistan levocetirizine was first launched in a liquid formulation by Novartis Consumer Health Division under the name of T-Day Syrup.
  • In Nepal levocetirizine is available in tablet with brand name Curin manufactured by Beximco Pharma.[2]
  • In Chile, it is marketed as Zival and made by Laboratorio Saval.
  • In Sweden, Xyzal was not granted subventions, and was withdrawn from the market.[3]

Side effects[edit]

Levocetirizine is called a non-sedating antihistamine as it does not enter the brain in significant amounts, and is therefore unlikely to cause drowsiness. However, some people may experience some slight sleepiness, headache, mouth dryness, lightheadedness, vision problems (mainly blurred vision), palpitations and fatigue.[4]

Research[edit]

Latest research shows levocetirizine reduces asthma attacks by 70% in children.[5]

Availability[edit]

The drug is currently available by prescription in the United States. Although the drug was only authorized by the FDA on 25 May 2007, it was already available in most European countries. Like many new drugs it entered the market at a higher price than currently available third and second generation antihistamines. In India, one form of the drug is available as Crohist MK tablets and syrup, a formulation of levocetirizine hydrochloride and montelukast. In India, Crohist MK is a Schedule 'H' drug and may only be prescribed by a registered medical practitioner. In Finland, Hungary, China, and Kuwait[6] the drug is sold over-the-counter.

Different brands (Actavis, Glenmark, UCB) Levocetirizine tablets and oral solution.

References[edit]

  1. ^ Grant, JA; Riethuisen, JM; Moulaert, B; DeVos, C; Gamalero, C.; Descalzi, D.; Folli, C.; Passalacqua, G.; Canonica, G.W. (February 2002). "A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects". Ann Allergy Asthma Immunol. 88 (2): 190–197. doi:10.1016/S1081-1206(10)61995-3. PMID 11868924. 
  2. ^ http://web.archive.org/web/20121022184859/http://beximco-pharma.com/allergic-disorders/147-curin.html. Archived from the original on October 22, 2012. Retrieved August 29, 2012.  Missing or empty |title= (help)
  3. ^ http://www.fass.se/LIF/substance?substanceId=ID11EHWRUFGBA53CSR
  4. ^ XOZAL technical specifications booklet.
  5. ^ Pasquali, M; Baiardini, I; Rogkakou, A; Riccio, AM; Gamalero, C; Descalzi, D; Folli, C; Passalacqua, G; Canonica, GW (September 2006). "Levocetirizine in persistent allergic rhinitis and asthma: effects on symptoms, quality of life and inflammatory parameters". Clinical & Experimental Allergy. 36 (9): 1161–7. doi:10.1111/j.1365-2222.2006.02548.x. PMID 16961716. 
  6. ^ On different names: http://www.hazipatika.com/gyogyszerkereso/termek/sefaller_5_mg_filmtabletta/54120

External links[edit]